KSBB Journal

  • 제27권3호
  • /
  • Pages.167-171
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  • 2012
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  • 1225-7117(pISSN)
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  • 2288-8268(eISSN)
한국생물공학회 (The Korean Society for Biotechnology and Bioengineering)
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아미노산 에스테르의 벤조피논 이민 유도체의 액체 크로마토그래피의 광학분리

Liquid Chromatographic Resolution of α-Amino Acid Esters as Benzophenone Imine Derivatives

  • 윤원남 (조선대학교 약학대학 약학과) ;
  • 서문준 (조선대학교 약학대학 약학과) ;
  • 황호 (조선대학교 약학대학 약학과) ;
  • 이원재 (조선대학교 약학대학 약학과)
  • 투고 : 2012.05.23
  • 심사 : 2012.06.08
  • 발행 : 2012.06.30
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초록

A convenient liquid chromatographic enantiomer separation of several ${\alpha}$-amino acid esters as benzophenone Schiff base derivatives on covalently immobilized chiral stationary phases (CSPs) derived from polysaccharide derivatives was developed. The benzophenone imine derivatives of ${\alpha}$-amino acid esters were readily prepared by stirring benzophenone imine and the ${\alpha}$-amino acid ester hydrochloride salts in 2-propanol. The chromatographic conditions used on all CSPs were 0.5% or 5% 2-propanol/hexane (V/V) as the mobile phases at 1 mL/min of flow rate and UV 254 nm detection. The performance of Chiralpak IC among all CSPs was superior to that of the other CSPs for resolution of benzophenone imine derivatives of ${\alpha}$-amino acid esters. It is expected that the developed analytical method will be useful for enantiomer resolution of other ${\alpha}$-amino acid esters as benzophenone Schiff base derivatives.

키워드

참고문헌

  1. Subramanian, G. (Ed.) (2001) Chiral Separation Techniques: A practical approach second revised ed., VCH, Weinheim.
  2. Francotte, E. and W. Lindner (Ed.) (2006) Chirality in Drug Research, Wiley-VCH, Weinheim.
  3. Huang, H., J. Y. Jin, and W. Lee (2011) Chromatographic enantiomer separation and determination of optical purity for α-amino acid esters as 9-anthraldimine derivatives using polysaccharide based chiral columns. Kor. Soc. Biotech. Bioeng. J. 26: 139-142. https://doi.org/10.7841/ksbbj.2011.26.2.139
  4. Xu, W. J., J. Y. Jin, and W. Lee (2011) Enantiomer separation of chiral amino alcohols as 9-anthraldimine derivatives on coated and covalently bonded chiral stationary phases based on polysaccharide derivatives by high performance liquid chromatography. Kor. Soc. Biotech. Bioeng. J. 26: 323-327. https://doi.org/10.7841/ksbbj.2011.26.4.323
  5. Duchateau, A. L. L., J. J. Guns, R. G. R. Kubben, and A. F. P. van Tilburg (1994) High-performance liquid chromatography of diamine enantiomers as Schiff bases on a chiral stationary phase. J. Chromatogr. A. 664: 169-176. https://doi.org/10.1016/0021-9673(94)87004-7
  6. O'Donnell, M. J., and Polt, R. L. (1982) A mild and efficient route to schiff base derivatives of amino acids. J. Org. Chem. 47: 2663-2666. https://doi.org/10.1021/jo00134a030
  7. Greene, T. W. and P. G. M. Wuts (1999) Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, New York.
  8. Jin, J. Y., W. Lee, J. H. Park, and J. J. Ryoo (2006) Covalently bonded and coated chiral stationary phases derived from polysaccharide derivatives for enantiomer separation of N-fluorenylmethoxycarbonyl $\alpha$-amino acids with fluorescence detection. J. Liq. Chrom. & Rel. Tech. 29: 1793-1801. https://doi.org/10.1080/10826070600717007
  9. Jin, J. Y. and W. Lee (2008) Enantiomer separation of N-protected $\alpha$-amino acids on covalently immobilized cellulose tris (3,5-chlorophenylcarbamate) chiral stationary phase in HPLC. Bull. Kor. Chem. Soc. 29: 491-493. https://doi.org/10.5012/bkcs.2008.29.2.491
  10. Jin, J. Y., S. K, Bae, and W. Lee (2009) Comparative studies between covalently immobilized and coated chiral stationary phases based on polysaccharide derivatives for enantiomer separation of N-protected $\alpha$-amino acids and their ester derivatives. Chirality 21: 871-877. https://doi.org/10.1002/chir.20680

피인용 문헌

  1. Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns vol.28, pp.6, 2013, https://doi.org/10.7841/ksbbj.2013.28.6.423